Carbon Disulfide → 5-[2-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenyl]-1,3,4-oxadiazole-2(3H)-thione

HRID 466054Notes

Reaction equation

[OH-].[K+].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[CH:10]=[CH:11][C:12]([NH:14][NH2:15])=[O:13])([CH3:6])[CH3:5].[C:24](=S)=[S:25]>C(O)C>[CH3:21][C:20]([C:17]1[CH:16]=[C:9]([CH:10]=[CH:11][C:12]2[O:13][C:24](=[S:25])[NH:15][N:14]=2)[CH:8]=[C:7]([C:4]([CH3:3])([CH3:5])[CH3:6])[C:18]=1[OH:19])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium hydroxide (0.5 g, 0.0096 mole) is added in one portion to a stirred 0° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxycinnamic acid hydrazide (2.8 g, 0.0096 mole) and carbon disulfide (1.7 g, 0.022 mole) in absolute ethanol (15.0 ml). The resulting mixture is stirred 1.5 hours at 0° C. before heating to reflux for four hours. The solution is cooled and the solvent is removed in vacuo. The residue is dissolved in water (50 ml) and washed with ether (20 ml). The aqueous layer is made acidic with aqueous 2M HCl and the product extracted with a 1:1 mixture of ethyl acetate/ether. The combined organic extracts are washed with saturated aqueous NaCl and

Workup

temperaturebefore heating
temperatureto reflux for four hours
temperatureThe solution is cooled
customthe solvent is removed in vacuo
dissolutionThe residue is dissolved in water (50 ml)
washwashed with ether (20 ml)
extractionthe product extracted with a 1:1 mixture of ethyl acetate/ether
washThe combined organic extracts are washed with saturated aqueous NaCl

Sources & evidence

ORD record: ord-3b35b05e91da4db2b032b1bea3aa3323
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155122

Reaction notes

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